SU420167A3 - - Google Patents
Info
- Publication number
- SU420167A3 SU420167A3 SU1715352A SU1715352A SU420167A3 SU 420167 A3 SU420167 A3 SU 420167A3 SU 1715352 A SU1715352 A SU 1715352A SU 1715352 A SU1715352 A SU 1715352A SU 420167 A3 SU420167 A3 SU 420167A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- diacetyl
- acetyl
- new
- aminophenol
- cysteine
- Prior art date
Links
- 238000000034 method Methods 0.000 description 8
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical class NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- -1 acetanitrile Chemical compound 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 238000006664 bond formation reaction Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
СПОСОБ ПОЛУЧЕНИЯ ПРОИЗВОДНЫХ п-АМИНОФЕНОЛАMETHOD OF OBTAINING DERIVATIVES OF p-AMINOPHENOL
Насто щее изобретение относитс к способу получени новых производпы.х п-аминофенола об 1ей формулыThe present invention relates to a process for the preparation of new productions of p-aminophenol of formula 1
RO-C.H -NH-CO-CH-CHj-SRRO-C.H-NH-CO-CH-CHj-SR
II
NHCOCH,NHCOCH,
где R и :R - радикалы, и.меющие одиноковые или различные значени , и представл ют собой водород или СОСНз-группу. Новые производные п-аминофенола обладают ценными фармакологическими свойствами.where R and: R are radicals and have the same or different meanings, and are hydrogen or COCH3. New derivatives of p-aminophenol possess valuable pharmacological properties.
.Широко .известен жар-бодиимидный способ образовани пептидной св зи в м гких услови х , обладающий р дом преимуществ по сра1внению с другими.The heat-imimide method of peptide bond formation under mild conditions is well known, having several advantages over other ones.
Основыва сь на этом известном способе, предлагаетс способ получени новых фармакологич-еоки а.кт;И:В;ных 1вещест.в, обла.дающих ценными ювойствами. В соответствии с изобретением новый способ получени соединений приведенной общей фор.мулы, заключаетс в том, что соединение , где R имеет указанные значени , конденсируют при температурах ниже 10°С в среде таких органических растворителей, как тетрагидрофуран , ацетанитрил, зтилацетат, с :М,5-диац.етил-4-цистеином в присутствии такого агентаBased on this well-known method, a method is proposed for the production of new pharmacological ekok.a.A: I: V; neytsnye zvezhest.v, possessing valuable goods. In accordance with the invention, a new method for producing compounds of the above general formula consists in that the compound, where R has the indicated values, is condensed at temperatures below 10 ° C in an environment of organic solvents such as tetrahydrofuran, acetanitrile, ethyl acetate, s: M , 5-diacyl-4-cysteine in the presence of such an agent
конденсации, как карбодинмид, лредпочтительно дициклогоксилкарбодиимид; целевой продукт выдел ют известными приемами.condensation, like carbodin-imide, is preferably dicyclo-xylcarbodiimide; The target product is isolated by known techniques.
В тех случа х, когда в полученном соединении R-Н,,5-диацетил-Ь-цистеин-п-окснанилид или .5-диацетил-Ь-цнстеин-п-ацетоксна .нилид, лолучевный сли-саиныл: способом,подвергают гидролизу в услови х, обеспечивающих избирательное отщепление ацетильной группы, св занной с атомом серы, причем гидролиз провод т предпочтительно в присутствии этилата натри при комнатиоГ температуре , использу -)тилпв1,1й спирт в качестве растворител .In those cases when in the resulting compound RH, 5-diacetyl-L-cysteine-p-oxanilide or .5-diacetyl-L-cstein-p-acetoxn. Nilide, lucharynye sly-sainil: method, subjected to hydrolysis under conditions that allow the selective cleavage of the acetyl group bound to the sulfur atom, and the hydrolysis is preferably carried out in the presence of sodium ethylate at room temperature, using alcohol as the solvent.
По предлагаемому способу, можно в |ч пкцию с ,5-диацетил-1..-цнсте п;ом вводить паминофенол и затем ацетилировать гпдроксильную группу полученного таким соединени ири по.могц подход щего агента ацетилировани . нarIpч eп хлористого ацетн .а, в среде ичридина, получа Х,5-днацетилЬ-Цистеи .;мп-а11Стс- с1 -а: илил, -который может по..учен гаг.же пр .лой реакцией п- иетоксианьлкнл с 5-Д :ацетил-.-цистеи1:ом.According to the proposed method, it is possible to introduce pamino phenol into the pitch with, 5-diacetyl-1 ..- group; o enter pamino phenol and then acetylate the hydroxyl group of the compound irim thus obtained according to the proper acetylation agent. harpch ept acetyl chloride, in ichridine medium, to give X, 5-dna acetyl-Cistea.; mp-a11 Cts-c1-a: or the llyl, which can be studied by the same reaction with p-ittoxyl 5 with 5 -D: acetyl -.- cystei1: ohm.
Пример 1. .Б-диацетил-1.-цистеин-п-оксианилид .Example 1. B-diacetyl-1.-cysteine-p-oxyanilide.
К смеси, охлажденной до 0°С и состо щей из 20,5 г (0,1 1мол ) Ы,5-д.иа,цетил-Ь-цисте1И;на,To a mixture cooled to 0 ° C and consisting of 20.5 g (0.1-1 mol) S, 5-dIa, cetyl-L-cystyl;
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU1715352A SU420167A3 (en) | 1971-11-15 | 1971-11-15 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU1715352A SU420167A3 (en) | 1971-11-15 | 1971-11-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU420167A3 true SU420167A3 (en) | 1974-03-15 |
Family
ID=20493288
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1715352A SU420167A3 (en) | 1971-11-15 | 1971-11-15 |
Country Status (1)
| Country | Link |
|---|---|
| SU (1) | SU420167A3 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4440788A (en) * | 1980-05-13 | 1984-04-03 | Mitsubishi Chemical Industries, Limited | Cysteine derivatives |
-
1971
- 1971-11-15 SU SU1715352A patent/SU420167A3/ru active
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4440788A (en) * | 1980-05-13 | 1984-04-03 | Mitsubishi Chemical Industries, Limited | Cysteine derivatives |
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